Aziridine Opening via a Phenonium Ion Enables Synthesis of Complex Phenethylamine Derivatives

We report that the treatment of unsymmetrical 2,3-disubstituted aziridines with TiCl4 yields β-phenethylamine products via the intermediacy of a phenonium ion. Derivatization of the products obtained via this method is demonstrated. Computational analysis of the reaction pathway provides insight into the reaction mechanism, including the selectivity of the phenonium opening.

本研究报道，以四氯化钛(TiCl4)处理不对称2,3-二取代氮丙啶(aziridines)，可经由苯鎓离子(phenonium ion)中间体生成β-苯乙胺类产物。本研究验证了利用该方法得到的产物可开展衍生化反应。对反应路径的计算分析为该反应的机理（包括苯鎓离子开环的选择性）提供了深入见解。